Clopidogrel bisulfate → Clopidogrel

HRID 1401052Notes

Reaction equation

HRID 1401052 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:18][C:17]2[CH:19]=[CH:20][S:21][C:16]=2[CH2:15][CH2:14]1)[C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].OS(O)(=O)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:18][C:17]2[CH:19]=[CH:20][S:21][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[Cl:12])=[O:4]

Participants

4

Reactant 2

HCID 115366Clopidogrel bisulfateHCID 516892Sodium Bicarbonate

Product 1

HCID 60606ClopidogrelYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

A suspension of Clopidogrel hydrogen sulfate (330 gms) was stirred in dichloromethane (1950 ml) and subsequently basified with NaHCO3 solution (10%, 3300 ml). The mixture was stirred at 25 to 30° C. for about 10 minutes. The layers were separated and the aqueous layer was extracted with dichloromethane (325 ml.) and washed with water (1300 ml.). It was then dried over Na2SO4 and distilled off on a water bath at a temperature in the range from 50 to 55° C. to obtain Clopidogrel free base (250 gms).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (325 ml.)
  3. washwashed with water (1300 ml.)
  4. dry with materialIt was then dried over Na2SO4
  5. distillationdistilled off on a water bath at a temperature in the range from 50 to 55° C.

Sources & evidence

ORD record
ord-f1b04965a35149c1b9a9ed3586f85d1e
Source dataset
uspto-grants-2014_12
Patent number
US08907090B2

Reaction notes

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